3-quinolyl-substituted dihydropyridines, and their use in medicaments
AssigneeBayer Aktiengesellschaft
InventorsJ urgen Stoltefuss, Siegfried Goldmann, Alexander Straub, Martin Bechem, Rainer Gross, Siegbert Hebisch, Joachim H utter, Howard-Paul Rounding
Life of this patent
Estimating the term…
Abstract
This invention relates to 3-quinolyl-substituted dihydropyridine derivatives, such as ##STR1## or a pharmaceutically acceptable salt thereof. These compounds are used in treating cardiovascular disease.
Claims8
A 3-quinoline dihydropyridine of the formula ##STR120## in which R.sup.1 represents hydrogen, amino, cyano, formyl or trifluoromethyl, or represents a straight-chain or branched alkyl having up to 8 carbon atoms, which is optionally substituted by hydroxyl or by a group of the formula --NR.sup.6 R.sup.7, --O--CO--R.sup.8, --O--(CH.sub.2).sub.a --OR.sup.8 or --O--(CH.sub.2).sub.b --NR.sup.9 R.sup.10, wherein
- R.sup.6, R.sup.7, R.sup.9 and R.sup.10 are identical or different and denote hydrogen or straight-chain or branched alkyl having up to 6 carbon atoms,
- R.sup.8 and R.sup.8' are identical or different and denote straight-chain or branched alkyl having up to 6 carbon atoms, and
- a and b are identical or different and denote the number 2, 3, 4 or 5,
- R.sup.2 represents a group of the formula --CO--NR.sup.11 R.sup.12 or --CO--A--R.sup.13, wherein
- R.sup.11 and R.sup.12 are identical or different and denote hydrogen or a straight-chain, branched or cyclic, saturated or unsaturated hydrocarbon radical having up to 6 carbon atoms, which is optionally substituted by fluorine, chlorine, hydroxyl, phenyl or pyridyl, or
- denote phenyl or pyridyl, which are optionally substituted by fluorine or chlorine or by alkyl, alkoxy, alkylthio or alkoxycarbonyl having in each case up to 2 carbon atoms, trifluoromethyl or trifluoromethoxy,
- A denotes a direct bond or an oxygen atom,
- R.sup.13 denotes hydrogen, phenyl or pyridyl, which are optionally substituted by fluorine, chlorine, methyl, methoxy, methylthio, trifluoromethyl or trifluoromethoxy, or
- denotes a straight-chain or branched, saturated or unsaturated hydrocarbon radical having up to 8 carbon atoms, which is optionally interrupted up to twice in an identical or different manner by oxygen or by --CO--, --CO--NH--, --O--CO--, --CO--O--, --NH--CO--, --SO.sub.2 --NH--, --NH--SO.sub.2 --, --S(O).sub.e -- or --NR.sup.16 --, wherein
- e denotes the number 0, 1 or 2,
- R.sup.16 denotes hydrogen or phenyl, which is optionally substituted by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, or denotes a cyclic, straight-chain or branched, saturated or unsaturated hydrocarbon radical having up to 4 carbon atoms, which is optionally substituted by chlorine, fluorine or phenyl,
- and the hydrocarbon radical is optionally substituted up to twice in an identical or different manner by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, fluorine, chlorine, nitro, cyano, hydroxyl, --O--NO.sub.2, or straight-chain or branched alkylthio, alkoxy or acyloxy having in each case up to 4 carbon atoms or by phenyl, phenoxy, phenylthio or pyridyl, fluorine, chlorine, cyano, methyl, methoxy, methylthio, trifluoromethyl or trifluoromethoxy, or
- the hydrocarbon radical is optionally substituted by a group of the formula --CO.sub.2 --R.sup.17, --CONR.sup.18 R.sup.19, --NR.sup.20 R.sup.21, --NH--SO.sub.2 --X and/or --NR.sup.22 --CO.sub.2 R.sup.23, wherein
- R.sup.17 has the abovementioned meaning of R.sup.16 and is identical to or different from this and
- R.sup.18, R.sup.19, R.sup.20, R.sup.21, R.sup.22 and R.sup.23 have the abovementioned meaning of R.sup.11 and R.sup.12 and are identical to or different from these, and
- X denotes phenyl, which is optionally substituted by methyl,
- R.sup.5 represents a straight-chain or branched, saturated or unsaturated hydrocarbon radical having up to 10 carbon atoms, which is optionally interrupted by oxygen or sulphur, or a saturated or unsaturated cyclic hydrocarbon radical and wherein said hydrocarbon radicals are optionally substituted up to twice in an identical or different manner by cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, fluorine, chlorine, bromine, acyloxy having up to 2 carbon atoms, cyano or hydroxyl or by phenyl, phenyloxy or phenylthio, wherein said phenyl rings are optionally substituted up to twice in an identical or different manner by fluorine, chlorine, bromine, hydroxyl, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio or by a group of the formula --NR.sup.24 R.sup.25, wherein
- R.sup.24 have the abovementioned meaning of R.sup.11 and R.sup.12 and are identical to or different from these,
- or the hydrocarbon radical is optionally substituted by a group of the formula --CO.sub.2 --R.sup.26, --CONR.sup.27 R.sup.28, --NR.sup.29 R.sup.30, --NR.sup.31 --CO.sub.2 R.sup.32 or --NR.sup.33 --SO.sub.2 R.sup.34 wherein
- R.sup.26 has the abovementioned meaning of R.sup.16 and is identical to or different from this and
- R.sup.27, R.sup.28, R.sup.29, R.sup.30, R.sup.31, R.sup.32, R.sup.33 and R.sup.34 have the abovementioned meaning of R.sup.11 and R.sup.12 and are identical to or different from these, or
- R.sup.5 represents a group of the formula D--R.sup.35, wherein
- D denotes the CO or --S(O).sub.h group or an oxygen atom, wherein
- h denotes the number 0, 1 or 2, and
- R.sup.35 denotes phenyl which is optionally substituted up to twice in an identical or different manner by fluorine, chlorine, bromine, cyano or nitro or by straight-chain or branched alkyl, alkoxy, alkylthio, alkoxycarbonyl, halogenoalkyl, halogenoalkoxy or halogenoalkylthio having in each case up to 4 carbon atoms or amino or by C.sub.1 -C.sub.4 -mono- or -dialkylamino, or
- R.sup.35 denotes hydrogen or a straight-chain or branched, saturated or unsaturated hydrocarbon radical having up to 8 carbon atoms, which is optionally interrupted by oxygen or sulphur, and which is optionally substituted by fluorine, chlorine, phenyl, phenoxy or phenylthio, or
- is substituted by a group of the formula --NR.sup.36 R.sup.37, wherein
- R.sup.36 and R.sup.37 have the abovementioned meaning of R.sup.11 and R.sup.12 and are identical to or different from these,
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.